Tetrahydrofuran → 2-{3-[(1R,2R)-2-Carboxy-2-hydroxy-1-(2-trifluoromethyl-benzyl)-ethylcarbamoyl]-propyl}-benzoic Acid

HRID 2361122Notes

Reaction equation

HRID 2361122 reaction equation
C([O:3][C:4]([C@H:6]([OH:34])[C@H:7]([NH:19][C:20]([CH2:22][CH2:23][CH2:24][C:25]1[CH:33]=[CH:32][CH:31]=[CH:30][C:26]=1[C:27]([OH:29])=[O:28])=[O:21])[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]([F:18])([F:17])[F:16])=[O:5])C.C1COCC1.[OH-].[Na+]>CC(O)=O>[C:4]([C@H:6]([OH:34])[C@H:7]([NH:19][C:20]([CH2:22][CH2:23][CH2:24][C:25]1[CH:33]=[CH:32][CH:31]=[CH:30][C:26]=1[C:27]([OH:29])=[O:28])=[O:21])[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]([F:18])([F:17])[F:16])([OH:5])=[O:3]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 710736032-{3-[(1R,2R)-2-Ethoxycarbonyl-2-hydroxy-1-(2-trifluoromethyl-benzyl)-ethylcarbamoyl]-propyl}-benzoic acid

Product 1

HCID 710736272-{3-[(1R,2R)-2-Carboxy-2-hydroxy-1-(2-trifluoromethyl-benzyl)-ethylcarbamoyl]-propyl}-benzoic AcidYield 100%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2-{3-[(1R,2R)-2-Ethoxycarbonyl-2-hydroxy-1-(2-trifluoromethyl-benzyl)-ethylcarbamoyl]-propyl}-benzoic acid was combined with THF (5 mL) and 10 M aqueous NaOH (96 μL, 4.0 eq.). The reaction was stirred for 4 hours. Upon completion of the reaction was completed, AcOH (1.5 mL) was added and the product was purified by preparative HPLC to yield the title compound (10 mg, 100% purity). MS m/z [M+H]+ calc'd for C22H22F3NO6, 454.14. found 454.

Workup

  1. customthe product was purified by preparative HPLC

Sources & evidence

ORD record
ord-e08f6dff499540f6811b6b4a14f65f25
Source dataset
uspto-grants-2014_04
Patent number
US08686184B2

Reaction notes

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